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Neoglycopeptide Synthesis and Purification in Multi‐gram Scale: Preparation of O ‐(2,3,4,6‐tetra‐ O ‐acetyl‐β‐ D ‐galactopyranosyl)‐ N α ‐fluoren‐9‐yl‐methoxycarbonyl‐hydroxyproline and Its Use in the Pilot‐scale Synthesis of the Potent Analgesic Glycopeptide O 1.5 ‐β‐ D ‐galactopyranosyl[ D Met 2 , Hyp 5 ]enkephalinamide
Author(s) -
Torres Josep Lluís,
Clapés Pere
Publication year - 1997
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/(sici)1099-1387(199703)3:2<99::aid-psc89>3.0.co;2-f
Subject(s) - tetra , gram , chemistry , scale (ratio) , hydroxyproline , stereochemistry , combinatorial chemistry , biochemistry , medicinal chemistry , biology , physics , bacteria , genetics , quantum mechanics
The preparation of a β‐galactosylated hydroxyproline derivative and its use in the multi‐gram solid‐phase synthesis of the potent analgesic neoglycopeptide O 1.5 ‐β‐ D ‐galactopyranosyl[ D ‐Met 2 , Hyp 5 ]enkephalinamide is described in this paper. The most closely related impurities have been identified, isolated and characterized. Significant aspects of the synthesis and purification affecting yields and purity of both the building block and the target neoglycopeptide are discussed. © 1997 European Peptide Society and John Wiley & Sons, Ltd.